(E)-1-[2-(4-Chloro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

M Umadevi; V Saravanan; R Yamuna; A K Mohanakrishnan; G Chakkaravarthi

doi:10.1107/S1600536813031073

. 2013 Nov 16;69(Pt 12):o1784. doi: 10.1107/S1600536813031073

(E)-1-[2-(4-Chloro-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one

M Umadevi ^a, V Saravanan ^b, R Yamuna ^c,^*, A K Mohanakrishnan ^b, G Chakkaravarthi ^d,^*

PMCID: PMC4004433 PMID: 24860289

Abstract

In the title compound, C₂₅H₁₉ClN₂O₅S, the phenyl ring forms dihedral angles of 79.62 (12) and 80.02 (13)° with the indole ring system and the benzene ring, respectively. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring. In the crystal, molecules assemble into double layers in the ab plane via C—H⋯O interactions.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998 ▶); Srivastava et al. (2011 ▶). For related structures, see: Chakkaravarthi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C₂₅H₁₉ClN₂O₅S
M _r = 494.93
Triclinic,
a = 8.4658 (3) Å
b = 8.6643 (3) Å
c = 16.1126 (6) Å
α = 84.196 (2)°
β = 87.768 (3)°
γ = 79.541 (2)°
V = 1156.01 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.922, T _max = 0.943
25531 measured reflections
6333 independent reflections
4536 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.150
S = 1.03
6333 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813031073/tk5271sup1.cif

e-69-o1784-sup1.cif^{(29.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031073/tk5271Isup2.hkl

e-69-o1784-Isup2.hkl^{(303.7KB, hkl)}

Click here for additional data file.^{(8.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813031073/tk5271Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1ⁱ	0.93	2.60	3.327 (3)	136
C16—H16B⋯O5ⁱⁱ	0.97	2.37	3.260 (3)	152

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

supplementary crystallographic information

1. Introduction

2. Experimental

2.1. Synthesis and crystallization

A solution of 1-(2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl)propan-1-one (5 g, 12.31 mmol) and triphenylphosphine (3.5 g, 13.54 mmol) in dry THF (100 ml) was refluxed for 6 h. After consumption of the starting material, the solvent was removed under vacuum and the solid washed with diethyl ether to give the phosphonium salt. Then, the mixture of phosphonium salt (8 g, 11.97 mmol), 4-chloro-2-nitrobenzaldehyde (2.45 g, 13.17 mmol) and K₂CO₃ (3.30 g, 23.95 mmol) in DCM (70 ml) was stirred at room temperature for 24 h. After completion of the reaction (monitored by TLC), it was diluted using DCM (30 ml), washed with water (2 x 100 ml) and dried (Na₂SO₄). Removal of solvent in vacuo followed by trituration of the crude product with MeOH (20 ml) afforded the title compound.

2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically and refined using riding model, with C—H = (0.93–0.97) Å and U_iso(H) = 1.2–1.5U_eq(C). Owing to poor agreement, the (001) reflection was omitted from the final cycles of refinement.

3. Results and discussion

In continuation of our studies on indole derivatives which are known to exhibit anti-microbial, anti-biotic, analgesic and anti-cancer activities (Okabe and Adachi, 1998; Srivastava et al., 2011), we herewith report the crystal structure of the title compound (I). The geometric parameters of (I) (Fig. 1) are in close agreement with similar structures (Chakkaravarthi et al., 2008; 2010).

The phenyl ring makes the dihedral angle of 79.62 (12)° with the indole ring system. The phenyl ring (C1—C6) and the benzene ring (C20—C25) are inclined at an angle of 80.02 (13)°. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring (C20—C25). The N1 atom is sp² hybridised as the bond angles around N1 atom sum 352.4°. Details of the C—H···O interactions are given in Table 2 - these lead to layers in the ab plane.